EP0801518A2 - Organische elektrolumineszente Vorrichtung - Google Patents

Organische elektrolumineszente Vorrichtung Download PDF

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Publication number
EP0801518A2
EP0801518A2 EP97302507A EP97302507A EP0801518A2 EP 0801518 A2 EP0801518 A2 EP 0801518A2 EP 97302507 A EP97302507 A EP 97302507A EP 97302507 A EP97302507 A EP 97302507A EP 0801518 A2 EP0801518 A2 EP 0801518A2
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EP
European Patent Office
Prior art keywords
organic
layer
cathode
transporting layer
luminescent layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP97302507A
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English (en)
French (fr)
Other versions
EP0801518B1 (de
EP0801518A3 (de
Inventor
Norikazu Nakamura
Keiichi Miyairi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shinko Electric Industries Co Ltd
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Shinko Electric Industries Co Ltd
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Publication date
Application filed by Shinko Electric Industries Co Ltd filed Critical Shinko Electric Industries Co Ltd
Publication of EP0801518A2 publication Critical patent/EP0801518A2/de
Publication of EP0801518A3 publication Critical patent/EP0801518A3/de
Application granted granted Critical
Publication of EP0801518B1 publication Critical patent/EP0801518B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/917—Electroluminescent

Definitions

  • the present invention relates to an organic EL device and, in more detail, it relates to an organic EL device comprising, between a cathode and an anode, a hole transporting layer and an organic luminescent layer which comprises an organic compound.
  • a conventional two layer type EL device having, between a cathode 100 and an anode 104 formed on a glass plate 102, a luminescent layer 108 composed of a luminescent material which exhibits electroluminescence when a voltage is applied thereto and a hole transporting layer 106 which transports holes generated in the anode 104 smoothly to the luminescent layer 108, has been used in a backlight for the display of an OA machine such as a word processor, for an automobile meter, and the like.
  • an inorganic compound has conventionally been used as the luminescent material for such an EL device, a high driving voltage has been required when the inorganic compound for the EL device is caused to emit high-intensity light.
  • An organic EL device having a luminescent layer composed of such an organic compound can be driven at a low voltage compared with an EL device having a luminescent layer composed of a conventional inorganic compound.
  • Japanese Unexamined Patent Publication No. 8-81472 discloses a three layer type EL device having a luminescent layer composed of 2-(O-hydroxyphenyl)-benzoxazole or -benzothiazole zinc complex, a three layer type organic EL device having an electron transporting layer composed of such a zinc complex as mentioned above has not been known.
  • An object of the present invention is to provide a three layer type EL device capable of emitting light of high intensity compared with conventional organic EL devices.
  • a three layer type organic EL device which is provided with an electron transporting layer comprising 2-(O-hydroxyphenyl)-benzoxazole or -benzothiazole zinc complex between a cathode and an organic luminescent layer is capable of emitting light of high intensity compared with a two layer type organic EL device which is not provided with such an electron transporting layer.
  • the present invention has thus been achieved.
  • the present invention provides an organic EL device which includes an organic luminescent layer comprising an organic compound and a hole transporting layer between a cathode and an anode, wherein said organic EL device comprises between said cathode and said organic luminescent layer an electron transporting layer comprising a zinc complex of the formula wherein X represents S or O.
  • Fig. 1 is a drawing for explanation of an embodiment of an organic EL device according to the present invention.
  • Fig. 2 is a mass spectrogram of 2-(O-hydroxyphenyl)benzothiazole zinc complex.
  • Fig. 3 is a graph illustrating the degree of luminance of the organic EL device of the present invention and that of a conventional organic EL device.
  • Fig. 4 is a mass spectrogram of 2-(O-hydroxyphenyl)benzoxazole zinc complex.
  • Fig. 5 is a drawing for explanation of a conventional organic EL device.
  • An organic EL device which emits green light of high intensity is obtained in the present invention when the EL device has an organic luminescent layer comprising quinolinol aluminum complex of the formula
  • Examples of the luminescent materials used in the organic luminescent layer may include quinolinol zinc complex, phorphiline zinc complex, azomethine zinc complex, and the like in addition to the quinolinol aluminum complex mentioned above.
  • Examples of the materials used in the hole injection layer may include pirazoline dimer, polyvinylcarbazole, and the like in addition to the tetraphenyldiamine derivative mentioned above.
  • the organic EL device according to the present invention can emit light of high intensity compared with conventional two layer type organic EL devices for reasons as described below.
  • a hole transporting layer is provided between the anode and the luminescent layer in order to transport the holes generated in the anode to the luminescent layer smoothly.
  • an electron transporting layer composed of a zinc complex represented by the formula (I) is provided between the cathode and the fluorescent layer in order to transport the electrons generated in the cathode to the luminescent layer smoothly.
  • the electrons generated in the cathode and the holes generated in the anode are likely to be easily transported to and injected into the luminescent layer through the electron transporting layer and the hole transporting layer, respectively, to enhance the densities of the electrons and the holes therein.
  • the efficiency of recombining the electrons and the holes is enhanced, and the EL device may thus emit light of high intensity.
  • the organic EL device of the present invention is a three layer type in which a hole transporting layer 16, a luminescent layer 18 and an electron transporting layer 20 are laminated in order between a cathode 10 composed of aluminum and a transparent anode 14 composed of indium-tin oxide (ITO) on a transparent glass plate 12, to the anode 14.
  • a hole transporting layer 16 composed of aluminum
  • a transparent anode 14 composed of indium-tin oxide (ITO) on a transparent glass plate 12, to the anode 14.
  • ITO indium-tin oxide
  • the cathode 10 has a thickness of 100 nm, and the hole transporting layer 16, the luminescent layer 18 and the electron transporting layer 20 each have a thickness of 75 nm.
  • the electron transporting layer 20 shown in Fig. 1 comprises the zinc complex of the formula (I).
  • the zinc complex of the formula (I) used in the present invention can be obtained by reacting a compound of the formula wherein X is S or O, with zinc acetate.
  • the reaction may be carried out by adding a solution of zinc acetate to a solution of the compound of the formula (IV) in a solvent such as methanol, and stirring the mixture at a specified temperature for a specified period of time.
  • a solvent such as methanol
  • the luminescent layer 18 of the three layer type organic EL device shown in Fig. 1 comprises quinolinol aluminum complex of the formula (II).
  • the hole transporting layer 16 of the organic EL device in Fig. 1 comprises the tetraphenyldiamine derivative of the formula (III).
  • a polycarbonate or polyvinylcarbazole may also be used in place of the compound of the formula (III) as a compound which may comprise the hole transporting layer 16.
  • the hole transporting layer 16, the luminescent layer 18 and the electron transporting layer 20 are each formed by vacuum deposition on the transparent anode 14 composed of indium-tin oxide (ITO) on the transparent glass plate 12 to give the organic EL device.
  • ITO indium-tin oxide
  • each layer is formed by continuous deposition in a high vacuum of about 10 -6 Torr without interrupting the vacuum state.
  • the luminescent material of the luminescent layer 18 is excited and emits light when a direct current or pulse voltage is applied from an electric source to the cathode 10 and the anode 14.
  • Such a three layer type organic EL device according to the present invention exhibits a significantly improved luminance compared with the conventional two layer type EL device including the hole transporting layer 16 and the luminescent layer 18 alone between the cathode 10 and the anode 14.
  • a two layer type organic EL device in which a luminescent layer composed of 2-(O-hydroxyphenyl)benzothiazole zinc complex is used has been proposed in Nikkei Microdevices, Feb. (1996).
  • the electron transporting layer 20 composed of the 2-(O-hydroxyphenyl)benzothiazole zinc complex of the three layer type organic EL device according to the present invention emits no light even when a voltage is applied to the anode 14 and the cathode 10. It is a layer which acts to move the electrons of the cathode 10 to the luminescent layer 18 smoothly. Accordingly, the three layer type organic EL device according to the present invention is different from the two layer type organic EL device described in Nikkei Microdevices.
  • the resultant solution in methanol was stirred for 1 hour and 45 minutes while being held at 50°C, followed by filtering out the precipitate.
  • the precipitate obtained by filtering was successively washed with water, a saturated solution of sodium bicarbonate and methanol, and finally washed with hexane, followed by drying in vacuum.
  • the yield of the product was 316 mg (59%), and its melting point was 304°C (DSC measurement).
  • a three layer type organic EL device 10 shown in Fig. 1 was prepared by forming in order, on a transparent anode 14 (indium-tin oxide) having a thickness of 100 nm and formed on a transparent glass plate 12, a hole injection layer 16 having a thickness of 75 nm and composed of a tetraphenyldiamine derivative, a luminescent layer 18 having a thickness of 75 nm and composed of quinolinol aluminum complex, an electron transporting layer 20 having a thickness of 75 nm and composed of the 2-(O-hydroxyphenyl)benzothiazole zinc complex synthesized in (1) and a cathode 10 having a thickness of 100 nm and composed of aluminum.
  • a transparent anode 14 indium-tin oxide
  • a hole injection layer 16 having a thickness of 75 nm and composed of a tetraphenyldiamine derivative
  • a luminescent layer 18 having a thickness of 75 nm and composed of quinolinol aluminum complex
  • the hole transporting layer 16, the luminescent layer 18, the electron transporting layer 20 and the cathode 10 were each formed by vacuum deposition.
  • the hole transporting layer 16, the luminescent layer 18 and the electron transporting layer 20 were formed by continuous deposition in a high vacuum of about 10 -6 Torr without interrupting the vacuum state. Consequently, the hole transporting layer 16, the luminescent layer 18 and the electron transporting layer 20 each had the same area.
  • a two layer type organic EL device shown in Fig. 5 was prepared in the same manner as in Example 1 except that the electron transporting layer 20 was not provided.
  • the two layer type organic EL device was prepared by forming in order, on a transparent anode 104 (indium-tin oxide) having a thickness of 100 nm and formed on a transparent glass plate 102, a hole transporting layer 106 having a thickness of 100 nm and composed of a tetraphenyldiamine derivative, a luminescent layer 108 having a thickness of 100 nm and composed of quinolinol aluminum complex and a cathode 100 having a thickness of 100 nm and composed of a metal such as aluminum.
  • a transparent anode 104 indium-tin oxide
  • a hole transporting layer 106 having a thickness of 100 nm and composed of a tetraphenyldiamine derivative
  • a luminescent layer 108 having a thickness of 100 nm and composed of quinolinol aluminum complex
  • a cathode 100 having a thickness of 100 nm and composed of a metal such as aluminum.
  • the three layer type organic EL device shown in Fig. 1 and comprising an electron transporting layer 20 composed of the 2-(O-hydroxyphenyl)benzothiazole zinc complex can emit light of high intensity compared with the two layer type organic EL device shown in Fig. 5 and not comprising an electron transporting layer 20.
  • a three layer type organic EL device having between the cathode and the luminescent layer, an electron injection layer composed of 2-(O-hydroxyphenyl)benzoxazole zinc complex showing a main peak near a mass number 485 in a mass spectrogram shown in Fig. 4, in place of the electron transporting layer 20 composed of the 2-(O-hydroxyphenyl)benzothiazole zinc complex in Example 1 was prepared.
  • the three layer type organic EL device thus prepared emitted light of high intensity compared with the two layer type organic EL device prepared in Comparative Example.
  • the three layer type organic EL device of the present invention can emit light of high intensity compared with the conventional two layer type organic EL device, it can be used for a display of an OA machine, and the like.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Luminescent Compositions (AREA)
EP97302507A 1996-04-11 1997-04-11 Organische elektrolumineszente Vorrichtung Expired - Lifetime EP0801518B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP8089432A JPH09279134A (ja) 1996-04-11 1996-04-11 有機ｅｌ素子
JP89432/96 1996-04-11
JP8943296 1996-04-11

Publications (3)

Publication Number Publication Date
EP0801518A2 true EP0801518A2 (de) 1997-10-15
EP0801518A3 EP0801518A3 (de) 1998-04-22
EP0801518B1 EP0801518B1 (de) 2001-06-27

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP97302507A Expired - Lifetime EP0801518B1 (de) 1996-04-11 1997-04-11 Organische elektrolumineszente Vorrichtung

Country Status (6)

Country Link
US (1) US5922480A (de)
EP (1) EP0801518B1 (de)
JP (1) JPH09279134A (de)
KR (1) KR100258776B1 (de)
DE (1) DE69705345T2 (de)
HK (1) HK1001539A1 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000058315A1 (en) * 1999-03-31 2000-10-05 Lg Chemical, Ltd. Organometallic complex molecule and organic electroluminescent device using the same
WO2003018712A1 (en) * 2001-08-31 2003-03-06 Neoview Co., Ltd. Organic luminescent compound and organic light-emitting device using the same
WO2009061233A1 (fr) * 2007-11-08 2009-05-14 Institut Problem Khimicheskoi Fiziki Rossisskoi Akademii Nauk (Ipkhf Ran) Matériau électroluminescent contenant une substance luminescente organique
CN103146377A (zh) * 2013-03-20 2013-06-12 北京师范大学 金属配合物荧光薄膜的水热原位生长制备方法

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US6465116B1 (en) 1998-06-08 2002-10-15 Nec Corporation Organic electroluminescent device
US6699594B1 (en) 1998-06-08 2004-03-02 Nec Corporation Organic electroluminescent device
KR100937900B1 (ko) * 2001-08-29 2010-01-21 유니버시티 오브 서던 캘리포니아 금속착물을 포함하는 캐리어수송층을 구비한 유기발광장치
JP4643079B2 (ja) * 2001-09-11 2011-03-02 シャープ株式会社 電界発光素子
KR100989817B1 (ko) * 2007-07-24 2010-10-29 다우어드밴스드디스플레이머티리얼 유한회사 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기 전계 발광 소자
JP5669346B2 (ja) * 2007-07-24 2015-02-12 グレイセル・ディスプレイ・インコーポレーテッドＧｒａｃｅｌ Ｄｉｓｐｌａｙ Ｉｎｃ． 新規な赤色エレクトロルミネッセンス化合物およびそれを使用した有機エレクトロルミネッセンスデバイス
KR100850886B1 (ko) * 2007-09-07 2008-08-07 (주)그라쎌 전기발광용 유기금속 화합물 및 이를 발광재료로 채용하고있는 표시소자
KR100923655B1 (ko) * 2007-11-02 2009-10-28 (주)그라쎌 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자
KR100933229B1 (ko) * 2007-11-12 2009-12-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자
KR100933228B1 (ko) * 2007-11-15 2009-12-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자
KR100933226B1 (ko) * 2007-11-20 2009-12-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자
KR100910153B1 (ko) * 2007-11-20 2009-07-30 (주)그라쎌 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자
KR100910151B1 (ko) * 2007-11-22 2009-07-30 (주)그라쎌 신규한 유기 발광 화합물 및 이를 발광재료로 채용하고있는 전기발광소자
KR100933225B1 (ko) * 2007-11-27 2009-12-22 다우어드밴스드디스플레이머티리얼 유한회사 신규한 인광 화합물 및 이를 발광재료로서 채용하고 있는유기발광소자
KR100970713B1 (ko) * 2007-12-31 2010-07-16 다우어드밴스드디스플레이머티리얼 유한회사 유기발광화합물을 발광재료로서 채용하고 있는 전기 발광소자
KR100966886B1 (ko) * 2008-01-29 2010-06-30 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자
KR100966885B1 (ko) * 2008-02-29 2010-06-30 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전계 발광 소자
KR100946409B1 (ko) * 2008-03-19 2010-03-09 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전계 발광 소자
GB0814954D0 (en) * 2008-08-18 2008-09-24 Oled T Ltd Compounds having electron transport properties and their preparation and use
JP6060361B2 (ja) * 2011-08-03 2017-01-18 株式会社Ｊｏｌｅｄ 有機発光素子

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000058315A1 (en) * 1999-03-31 2000-10-05 Lg Chemical, Ltd. Organometallic complex molecule and organic electroluminescent device using the same
WO2003018712A1 (en) * 2001-08-31 2003-03-06 Neoview Co., Ltd. Organic luminescent compound and organic light-emitting device using the same
WO2009061233A1 (fr) * 2007-11-08 2009-05-14 Institut Problem Khimicheskoi Fiziki Rossisskoi Akademii Nauk (Ipkhf Ran) Matériau électroluminescent contenant une substance luminescente organique
CN103146377A (zh) * 2013-03-20 2013-06-12 北京师范大学 金属配合物荧光薄膜的水热原位生长制备方法
CN103146377B (zh) * 2013-03-20 2014-06-04 北京师范大学 金属配合物荧光薄膜的水热原位生长制备方法

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KR100258776B1 (ko) 2000-06-15
DE69705345D1 (de) 2001-08-02
EP0801518B1 (de) 2001-06-27
US5922480A (en) 1999-07-13
KR970071947A (ko) 1997-11-07
HK1001539A1 (en) 1998-06-26
DE69705345T2 (de) 2001-10-31
EP0801518A3 (de) 1998-04-22
JPH09279134A (ja) 1997-10-28

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